


Looking for a Good Time

by thewinchesterlifestyle



Category: Supernatural
Genre: Bottom Dean, Cock Slut Dean, Dean/OMC - Freeform, Dildos, Grace-Powered Orgasms, Jealous Castiel, M/M, One Night Stands, Possessive Castiel, Rough Sex, Size Kink, Slut Dean, Teasing, Top Castiel
Language: English
Status: Completed
Published: 2017-04-24
Updated: 2017-04-24
Packaged: 2018-10-23 09:26:55
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,802
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10716669
Author URL: https://archiveofourown.org/users/thewinchesterlifestyle/pseuds/thewinchesterlifestyle
Summary: It had been awhile since he’d left a bar with a guy but Dean had been itching for a long, hard night of sex and he had faith this particular guy was going to give him exactly what he wanted.





	Looking for a Good Time

**Author's Note:**

> Written for a prompt.

Dean grinned as he slid off the bar-stool, flashing a quick grin at Castiel when he knew he’d gotten lucky, before he was following the guy that had spent an hour flirting with him out the door. The first thing he’d noticed about the guy had been his hands, next the guy’s muscles and then the handsome features.

The guy had hit every single one of Dean’s requirements for a good fuck and it really didn’t hurt that he’d caught the outline of an impressive cock in the guy’s pants. Dean was more than sure this guy knew how to fuck and knew exactly what to do with Dean so he’d be leaving well fucked in the morning.

It had been awhile since he’d left a bar with a guy but Dean had been itching for a good, hard fucking and he had faith _this_ particular guy was going to give him exactly what he wanted.

They headed back to the guy’s apartment, Matt he’d told Dean at the bar, before stumbling back to the bedroom. Dean grinned when his shirt was thrown carelessly across the room and strong hands gripped him to slam him against the wall so warm lips could crash against his own.

The warm weight of a strong body against his own was turning him on and he moved his hand up to grip the guy’s hair. He could feel how his hardening cock was pressing against his pants and groaned when Matt ground their hard-ons together. “I hope you’re going to make me feel this tomorrow.” He smirked against Matt and watched the challenge light up grey eyes. Dean was looking forward to seeing if Matt rose to the challenge. “I’d hate to have picked wrong. There was that one guy—”

“You’re going to be feeling me for  _days_ , green eyes. I’m going to fuck that tight ass of yours until you’re sloppy and gaping. Then I’m going to fuck you again and again.” The comment about his eyes had Dean arching a brow until the expression as wiped off his face when he was jerked from the wall. “I knew I was fucking you tonight the second I laid eyes on you. Knew I was going to be buried balls deep in your round ass by the end of the night.”

“That confident?” Dean grinned as he started working Matt’s pants off. He watched Matt nod and jerked his pants down before glancing up. Dean  _knew_  about his looks and he had absolutely no problem utilizing them to manipulate his fuckbuddy for the night.

He also knew exactly how fuckable his ass looked. Every single guy he’d let fuck him always had nothing but praise for him.

It didn’t take long before he was being hauled up and dragged towards the bed, pushed down so he fell onto the mattress with a slight bounce. Matt wasted no time stripping the rest of his clothes off and then removing his own so he could press Dean down with his body.

Dean had managed to catch sight of the monster between Matt’s legs and almost moaned out loud at the very thought of that thing buried inside of him, fucking and filling him up.

 “Of course.” Matt bit down against Dean’s collarbone and smirked when it had Dean, pressed under him, shuddering out a rough moan. “Like a little pain with your pleasure?” he reached between them to simply grip Dean’s cock. “Think I’ll prep you just enough so you can ride that wave of pain and pleasure while I fuck you.”

“You know what I like more?” Dean asked as he hooked his legs around Matt’s waist, “Getting fucked.” He tightened his grip with his legs and watched the face above him. “How about it? Going to actually use that monster or are you just going to talk about it?”

Matt pulled back to grab some lube while Dean scooted up on the bed. He watched Matt open the lube before he was being pushed so Matt could start opening him up. Dean ended up face down, knees spread wide and ass raised up with his back bowed. Mattwas quick and efficient only teasing Dean’s prostate until he was pumping three fingers inside.

It wasn’t as thorough as a prep job meant to full loosen his hole but it was enough Dean wasn’t going to worry about too much pain.

“Come on.” Dean clenched around him and moaned at the fingers moving inside him as he shoved himself back into Matt’s fingers, “Put that dick between your legs to work.”

“I plan on putting it to work a few times. You think I’m going to let you out of my bed after only one fuck?” fingers slipped from Dean as Matt stroked himself and slicked his thick cock up so he could start guiding himself inside Dean again.

He pressed in inch by inch, Dean’s aching hole spreading wide open, until Matt could press Dean into the sheets with his whole body, hands grabbing Dean’s wrists to pin them down. Heavy balls rested against Dean’s ass as he shuddered at the completely full feeling and the burn of too much stretch. It wasn’t long after before Matt started moving. The bed groaned softly at the movements of Matt’s hips thrusting forward and the power behind each snap of his hips, “Going to bend your pretty ass over the bed next and fuck you hard.”

Dean clenched down on Matt and pushed up against his body in response with a wicked light to his eyes when he glanced back. “ _Good_.”

The rhythmic slap of skin against skin filled the room along with their moans as Matt’s pace increased until he was brutally slamming into Dean’s ass.

“Fuck fuck fuck.” Dean’s cheeks flushed with his pleasure as his fingers curled in the sheets and his ass shoved back to take Matt balls deep with every single thrust. “Ooohh fuck. Fuck that feels…fuck fuck right there yesss ohh oh ohh yes!”

Matt grunted as he continued to pound into Dean’s ass, thick cock pumping swiftly into Dean, as the headboard started to rap against the wall. “Love your ass. Fuck. You feel so fucking good. Knew you would. Knew you’d look perfect with my dick splitting your ass open.”

Dean tried to free a hand to reach under but Matt hauled his arms behind his back, pinning them with one hand, before he reached under to tease Dean.

“Fuck!” the word ripped out of him and Dean’s ass clenched as pleasure started to burn in his gut. His breathing shuddered and his mouth worked as his moans filled the room. His orgasm was pulled from him as Matt stroked him to his release and then Matt fucked him through his orgasm, pace falling off the closer he got to his own.

One, two, three more thrusts and then Matt was slamming deep, hips jerking, as his release emptied into Dean’s aching ass. “Shit.” The word was breathed out with a laugh, breathless and pleased, as Matt’s body draped over him and Dean panted on the bed.

“Good to know you know what to do with that unnatural monster you call a dick.”

Matt laughed lowly as he eased back and his softening cock slipped from Dean’s sore ass pulling a low hiss from him. “Good to know your ass is as fuckable as I thought.”

“My ass is _very_ fuckable.” Dean smirked as he glanced back at Matt, “So is my mouth.”

It earned him a matching smirk, “I bet.”

The next one was exactly as Matt said it would be: Dean draped over the side of the bed while Matt pounded into him viciously from behind only this time he’d allowed Matt to bind his wrists together with a tie.

By the end of it Dean had simply laid over the edge of the bed, gloriously fucked, as Matt’s release leaked from his puffy hole and Matt looked around for a toy to hold them over until they were ready for another round.

“I’m more than sure you can take this one.” Matt breathed out, “You look like the kind of bottom who is used to taking this kind of dildo.”

Dean caught sight of it and mentally groaned. He was going to be feeling that one for a few days. “You’re going to need a lot more lube for that.” But he wasn’t going to back down just because the toy was longer than anything he’d ever taken.

Matt added more lube, fingers fucking his ass a few times, before directly adding lube to his loose hole. Dean jerked at the feeling, hole clenching at the sensation, before he froze at the blunt pressure of the toy pressing against his ass.

“How big is that thing anyway?” he tried for nonchalant, voice rough and body trying not to tense, as the dildo pushed into him and his ass was forced to spread wide open. It burned as he pressed his face against the sheets, trying to steady his breathing, as Matt braced a hand on the small of his back while working the toy in.

There was a pause as Matt kept fucking the toy into him in short jabs that stole Dean’s breath and had his eyes clenching shut. He’d wanted a wild night where he could feel it for days later.

That was exactly what Matt was giving him.

“About three inches wide. I think this one might be about sixteen inches long.”

Dean mentally winced at the reality of the toy’s size but didn’t say anything. Instead he worked on relaxing and breathing through the toy pushing deep inside of him as his ass was forced to accommodate it.

“Not even my biggest toy but we don’t know each other well enough for that one.”

“But we know each other well enough for this one?” he moaned lowly as the toy pushed even deeper before it was pulled out, more lube added and Matt began pushing it back in once more.

Matt applied a bit more pressure and it sunk deeper than it had been. “You told me repeatedly exactly what you were hoping. We know each other well enough for this toy and I really wanted to see how gorgeous you’d look fucked full with it.”

It took awhile as Matt fucked the dildo into him until the base was resting flush against his ass and Dean was panting, muscles twitching under his skin and body tensed.

“Perfect.” Matt’s voice was rough and Dean knew he couldn’t talk without sounding completely wrecked. His ass felt like he’d been fucked by a group of men for hours, the ache undeniable, as Matt eased it out and then began to fuck him with it.

Dean whined at the sensation and when it brushed his prostate he jerked, cock aching where it rested between his stomach and the bed. Matt seemed completely content to fuck him repeatedly with the huge dildo, pumping it through the copious amounts of lube he’d had to add, as Dean moaned and gasped where he was still bent over.

“You’re so responsive.” Matt’s wrist rapidly moved and Dean’s hands twisted where they were bound. He wanted to shove himself into the toy, wanted to grip something but Matt had him completely at his mercy. “So gorgeous all fucked out.”

By the time Matt was ready for another round Dean couldn’t quite get his muscles to cooperate and ended up sprawled out on his back, legs draped over Matt’s shoulders, as Matt fucked him for the third time.

Dean could only lay there, moaning and begging, as Matt greedily fucked and fucked. The headboard was once more rapping against the wall, the mattress groaning at the strength behind Matt’s thrusts.

“Ohhh oh fuck oh oh there there yes. Fuck, Matt, holy fuck. So close.”

His mouth worked, his cheeks were flushed and his cock ached with the need to come as Matt fucked him. Matt’s eyes were dark, pupils disappearing the grey of his eyes, as he kept fucking. Dean didn’t know how long he could stand this, desperately wanting to touch himself but Matt had wanted to see him come on a cock alone.

“I know you can.” Matt’s voice was rough, sweat noticeable along his naked skin, as he kept snapping his hips forward. Dean wasn’t the only one suffering; Matt had put a cockring on himself to drag it out and Dean didn’t think he could take anymore of this. “Come on.”

He was almost to the point of begging, near sobbing with the need to come, when Matt finally fucked him to an untouched orgasm that had him howling and slumping back onto the sheets. Dean couldn’t have moved if he wanted as Matt pulled out, removed the cockring and slipped back in.

It only took two thrusts before he was coming with a deep moan of pleasure.

It was close to noon when Dean slipped out from under Matt’s arm. He moved across the room collecting his clothes and right out of the bedroom. Part of him wanted to stay for the morning fuck he’d been promised, the night beyond anything he could have hoped, but he wasn’t going to stay any later and he already had a very nice well fucked feeling to remember the night by.

Thinking about the mind blowing sex had him leaving a number behind because Matt was the kind of one-night-stand Dean would very happily return to for more.

His muscles ached, the pain in his ass had him limping and he felt deeply sated. It had been a very long time since he’d found someone who could live up to the promise of making him feel it for days. Dean was very sure he was going to be feeling that night for days.

Maybe he’d luck into stumbling across Matt again? Or get a call for another night of wild sex?

He couldn’t lose the satisfied grin when he stepped outside, climbed into his car and drove back to the room he was staying at. It was near impossible to remove it as he basked in the delightful feeling of the morning after a wild, enjoyable night.

Once he was inside his room he had every intention of taking a long hot shower, he’d gotten a workout most of the night, but the sight of an annoyed angel in the middle of his room stopped him. “Maybe if you got laid that pinched look wouldn’t be so permanent on your face. We’ll find you a nice girl to lose some of that tension with.” He wasn’t letting Castiel ruin the good feelings he was riding on but when he went to step around Castiel he was blocked. “ _What_?”

“Where were you?”

Dean furrowed his brow, “You were with me last night when I scored, Cas. I spent the night getting laid.” Now he grinned, “In multiple positions and with a truly memorable toy. You should have picked someone up yourself. You’re always wound so tight.” He patted Castiel on the shoulder and tried to move around him again.

“You spent the whole night with that man?”

“Yes.” Dean sighed and rocked back on his heels, “This isn’t news. I told you when we were going to the bar that I was looking for a good time. I _found_ a great time. Many, many times.”

Dean watched as Castiel crowded right into his space until he was backing up a few steps. A warm hand came down on his shoulder, over the place Castiel’s handprint used to show, as warmth wrapped around him. “What’s wrong with me?” Castiel demanded in a low measured voice. “Am I not a desirable partner?”

Dean blinked and his mouth dropped open in surprise. “ _Um_.” It was inelegant and Dean mentally smacked himself. “Well…you’re not really into that kind of thing and I—”

Castiel looked at Dean’s neck, at the marks he could see on the skin there, before growling lowly. The sound had Dean swallowing and shifting on his feet in surprise at the curl of arousal in his gut. That shouldn’t have sounded so arousing but his mind had been on a morning fuck. It was hard to get out of that mindset after hours of mind blowing sex. “Do you think I couldn’t,” there was a brief pause as though Castiel was weighing his next words, “ _Fuck_  you right?”

“Oh.” Dean felt himself hauled in for a rough kiss that had him _melting_  into Castiel. He could feel something warm moving through him, wrapping around everything he was, as the fingers locked down on him gripped a little tighter. Grace twisted through him, manipulating his body and causing him to go completely limp without thought.

When Castiel broke the kiss Dean’s cheeks were flushed, his lips swollen and his eyes were glazed. “I don’t like you sleeping with so many people. You’re mine.” The note of possession in Castiel’s tone had Dean’s eyes dilating and his hands gripping the trench coat Castiel wore. He’d always had a kink for possessive men and an even bigger one for manhandling. “To think that man got to touch you, to take you, all night…” he trailed off and Dean could  _see_  the jealousy there.

His cock was rock hard in his pants and aching as Castiel’s grace teased him into a frenzy.

One second they were standing in the middle of the room and the next Castiel was pressing him down against the mattress. “Woah.” Dean twisted under Castiel and gasped when he felt his angel’s erection pressing against him. This is a completely different level of manhandling.

* * *

Castiel ground himself down and relished the moan it pulled from  _his_  hunter. He could see the reactions to his touches and couldn’t stop the little bit of smugness at the thought that he was causing that instead of some nameless human.

It was impossible not to see the bruising, the smell the scent of some unknown human’s come deep inside of Dean, as he pressed Dean down into the mattress.

He wasn’t used to jealousy and it had quickly caused annoyance. Now he focused on sending pleasure through Dean’s body, pulling moans and  _whimpers_ , from Dean until he heard words instead of sounds. He might not be experienced in human sex but he’d seen enough observing humans and his grace could easily cause enough pleasure that Dean would forget that other human.

“Quit teasing.” Dean tugged on him and pressed himself up against Castiel’s pants covered cock. “Put that angel stamina to the test.” But he wasn’t done, “Are you going to make me regret picking Matt over you last night?”

That had a growl escaping and their clothes banished. Dean jerked at the sudden coolness against his skin and then he was squirming at the feeling of lube coating his insides. Castiel couldn’t help the amusement that filled him at the shock in Dean’s green eyes when he’d used grace to prep him.

“Fuck!” Dean twisted but it only had his cock rubbing against Castiel’s and he was focusing on that feeling instead. “Angels.” He muttered when his legs were being hitched over Castiel’s hips and Castiel’s cock was being guided inside him.

“Not wasting time.” Dean was clearly about to make a comment when Castiel buried himself inside him with a quick snap of his hips. It caused Dean’s mouth to drop open on a moan instead of the snarky comment Castiel knew he was about to say.

Dean was full and stretched; Castiel could see the thoughts dancing through Dean’s mind and the way Dean relished the feeling. He felt the way that Dean was trying to shove himself against Castiel, gripping his arms, as Castiel started to move. It was rough and hard and fast and Dean was  _moaning_  for more. Demanding more until the bed was slamming against the wall, almost cracking it with the force as Castiel worked to temper his strength.

It wouldn’t do to hurt or kill Dean if he lost control.

“Fuck. Fuck fuck fuck.” Dean managed, throat working, as he hung on and lost himself to the feeling of Castiel thrusting inside him and grace teasing him until he was burning with pleasure. “Oh there yes yes oh yes  _fuck_.”

The words fell away to babbling that Castiel seemed to understand as he shoved his face against Dean’s neck and kept slamming forward, careful to make sure he wasn’t harming Dean, as he worked them both towards their orgasms. He wanted to erase everything that  _Matt_  had done to Dean and replace it with himself. He wanted Dean to feel  _him_  with every step he took. He wanted his hunter to think of this moment and flush with arousal for  _him_  and no one else.

He was tired of watching Dean fall into bed with random people and come back to him with a sated grin reeking of various humans. Castiel was tired of all of it and he pressed his grace insistently against Dean’s prostate until Dean was coming between them with a high-pitched howl. He felt Dean shaking with his orgasm, shuddering, as he went limp and panted on the cool sheets.

“ _Cas_.” Dean gasped it out and clenched around Castiel as he kept rocking forward, still teasing Dean with grace, until his cock was spilling inside Dean. He pressed his lips against Dean’s shoulder, right above where his mark had been, before he shifted to press them against Dean’s lips.

“ _Mine_.” The possessive note was still there and Dean watched him glance back to his shoulder with a satisfied look on his features. Castiel watched as Dean turned his head to glance over and blinked at the sight of Castiel’s handprint once more branded into his skin.

“Fucking branded me again.” Dean gave him a slightly unimpressed look as he tugged at Castiel’s hair, “How am I going to explain that to the next person who sees me without my shirt?”

Castiel scowled at the thought. He could tell that Dean had seen this in much the same way he saw having sex with the countless humans he’d coupled with over the years. A bit of fun and release between two people.

Slowly Castiel eased out of Dean’s loose hole, cock now soft, as his release steadily leaked out of Dean’s gaping hole.

Dean simply grinned at him, sated and pleased, as he rested on the sheets and stared up at Castiel with a kind of softness that Castiel wished meant something _more_. At least he’d gotten this and he might get more of it in the future.

There were several times that Dean had fucked the same human on several different occasions.

**Author's Note:**

> Another fic where Dean is all about having good, and sometimes kinky, sex with no-strings-attached and poor Castiel is a bit in love with him.
> 
> It's a bit bittersweet at the end but Dean thoroughly enjoyed himself across the board, didn't he?


End file.
